NPASS Compound

Structure

CID64123 OpenBabel06191715402D 21 22 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 15 2 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 19 5 1 6 0 0 0 20 6 1 6 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.26
Volume:	340.881
LogP:	5.613
LogD:	4.406
LogS:	-5.736
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	4.271
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.675
MDCK Permeability:	1.1194508260814473e-05
Pgp-inhibitor:	0.53
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	90.92295837402344%
Volume Distribution (VD):	1.479
Pgp-substrate:	5.838639259338379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.25
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.313
CYP2C9-substrate:	0.537
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.756
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	7.169
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.475
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.348
Skin Sensitization:	0.934
Carcinogencity:	0.318
Eye Corrosion:	0.957
Eye Irritation:	0.893
Respiratory Toxicity:	0.955

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC64123

Natural Product ID:	NPC64123
*Common Name:**	Isoabienol
IUPAC Name:	(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-methylidenepent-4-enyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:
Standard InCHIKey:	JTWQQJDENGGSBJ-KVPLUYHFSA-N
Standard InCHI:	InChI=1S/C20H34O/c1-7-15(2)9-10-17-19(5)13-8-12-18(3,4)16(19)11-14-20(17,6)21/h7,16-17,21H,1-2,8-14H2,3-6H3/t16-,17+,19-,20+/m0/s1
SMILES:	C=CC(=C)CC[C@H]1[C@](C)(O)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228954
PubChem CID:	11220007
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO5326	Knema furfuracea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254357]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6066	Graphium sarpedon	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4903	Duroia hirsuta	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	0totodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5326	Knema furfuracea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT835	Organism	Gloeophyllum trabeum	Gloeophyllum trabeum	Inhibition	=	6.8	%	PMID[480865]
NPT2549	Organism	Laetiporus sulphureus	Laetiporus sulphureus	Inhibition	=	8.2	%	PMID[480865]
NPT834	Organism	Trametes versicolor	Trametes versicolor	Inhibition	=	27.8	%	PMID[480865]
NPT2550	Organism	Lenzites betulinus	Lenzites betulinus	Inhibition	=	25.6	%	PMID[480865]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC64123 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2030
0.2-0.3	10559
0.3-0.4	15541
0.4-0.5	7307
0.5-0.6	4863
0.6-0.7	1767
0.7-0.8	381
0.8-0.85	46
0.85-0.9	11
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC476431
0.9	High Similarity	NPC474769
0.9	High Similarity	NPC189290
0.8923	High Similarity	NPC94192
0.8871	High Similarity	NPC41160
0.8769	High Similarity	NPC88454
0.8769	High Similarity	NPC117607
0.8769	High Similarity	NPC101307
0.8667	High Similarity	NPC264779
0.8667	High Similarity	NPC39068
0.8636	High Similarity	NPC2648
0.8571	High Similarity	NPC63958
0.8529	High Similarity	NPC167706
0.8507	High Similarity	NPC210323
0.8507	High Similarity	NPC9942
0.8406	Intermediate Similarity	NPC182717
0.8358	Intermediate Similarity	NPC139785
0.8333	Intermediate Similarity	NPC476406
0.8333	Intermediate Similarity	NPC279434
0.8308	Intermediate Similarity	NPC101128
0.8286	Intermediate Similarity	NPC476366
0.8286	Intermediate Similarity	NPC201048
0.8281	Intermediate Similarity	NPC282694
0.8281	Intermediate Similarity	NPC79576
0.8281	Intermediate Similarity	NPC194208
0.8209	Intermediate Similarity	NPC185874
0.8209	Intermediate Similarity	NPC253303
0.8209	Intermediate Similarity	NPC269077
0.8209	Intermediate Similarity	NPC139207
0.8182	Intermediate Similarity	NPC258595
0.8143	Intermediate Similarity	NPC68443
0.8116	Intermediate Similarity	NPC475728
0.8116	Intermediate Similarity	NPC45296
0.8088	Intermediate Similarity	NPC244790
0.806	Intermediate Similarity	NPC473929
0.806	Intermediate Similarity	NPC149680
0.806	Intermediate Similarity	NPC42630
0.8056	Intermediate Similarity	NPC106432
0.8056	Intermediate Similarity	NPC470749
0.8056	Intermediate Similarity	NPC265588
0.803	Intermediate Similarity	NPC144650
0.803	Intermediate Similarity	NPC68656
0.8028	Intermediate Similarity	NPC243342
0.8028	Intermediate Similarity	NPC477138
0.8028	Intermediate Similarity	NPC91858
0.8028	Intermediate Similarity	NPC22134
0.8028	Intermediate Similarity	NPC100334
0.8028	Intermediate Similarity	NPC162164
0.8	Intermediate Similarity	NPC110799
0.8	Intermediate Similarity	NPC111234
0.8	Intermediate Similarity	NPC301226
0.7945	Intermediate Similarity	NPC470758
0.7945	Intermediate Similarity	NPC471798
0.7945	Intermediate Similarity	NPC470711
0.7941	Intermediate Similarity	NPC197805
0.7917	Intermediate Similarity	NPC291503
0.7917	Intermediate Similarity	NPC32832
0.7917	Intermediate Similarity	NPC3403
0.791	Intermediate Similarity	NPC208198
0.791	Intermediate Similarity	NPC60837
0.791	Intermediate Similarity	NPC2728
0.791	Intermediate Similarity	NPC11555
0.791	Intermediate Similarity	NPC282619
0.791	Intermediate Similarity	NPC172613
0.7887	Intermediate Similarity	NPC211009
0.7887	Intermediate Similarity	NPC471799
0.7857	Intermediate Similarity	NPC145498
0.7838	Intermediate Similarity	NPC285761
0.7826	Intermediate Similarity	NPC32055
0.7826	Intermediate Similarity	NPC276616
0.7826	Intermediate Similarity	NPC208999
0.7826	Intermediate Similarity	NPC245795
0.7808	Intermediate Similarity	NPC27765
0.7808	Intermediate Similarity	NPC129165
0.7808	Intermediate Similarity	NPC91573
0.7808	Intermediate Similarity	NPC265328
0.7808	Intermediate Similarity	NPC120098
0.7808	Intermediate Similarity	NPC470766
0.7808	Intermediate Similarity	NPC189883
0.7808	Intermediate Similarity	NPC134330
0.7808	Intermediate Similarity	NPC104806
0.7808	Intermediate Similarity	NPC290598
0.7808	Intermediate Similarity	NPC122418
0.7808	Intermediate Similarity	NPC30590
0.7808	Intermediate Similarity	NPC237460
0.7794	Intermediate Similarity	NPC286669
0.7794	Intermediate Similarity	NPC222366
0.7794	Intermediate Similarity	NPC476039
0.7794	Intermediate Similarity	NPC475897
0.7778	Intermediate Similarity	NPC71152
0.7778	Intermediate Similarity	NPC254509
0.7778	Intermediate Similarity	NPC471797
0.7778	Intermediate Similarity	NPC49168
0.7778	Intermediate Similarity	NPC25511
0.7778	Intermediate Similarity	NPC38426
0.7778	Intermediate Similarity	NPC472503
0.7778	Intermediate Similarity	NPC196358
0.7778	Intermediate Similarity	NPC145552
0.7778	Intermediate Similarity	NPC476736
0.7778	Intermediate Similarity	NPC192638
0.7778	Intermediate Similarity	NPC5046
0.7778	Intermediate Similarity	NPC62657
0.7778	Intermediate Similarity	NPC308440
0.7761	Intermediate Similarity	NPC225415
0.7746	Intermediate Similarity	NPC164022
0.7746	Intermediate Similarity	NPC475077
0.7746	Intermediate Similarity	NPC242001
0.7733	Intermediate Similarity	NPC291379
0.7733	Intermediate Similarity	NPC273410
0.7733	Intermediate Similarity	NPC80530
0.7703	Intermediate Similarity	NPC472805
0.7703	Intermediate Similarity	NPC91594
0.7703	Intermediate Similarity	NPC157996
0.7703	Intermediate Similarity	NPC40394
0.7703	Intermediate Similarity	NPC34177
0.7703	Intermediate Similarity	NPC169994
0.7703	Intermediate Similarity	NPC132542
0.7703	Intermediate Similarity	NPC101475
0.7703	Intermediate Similarity	NPC90979
0.7692	Intermediate Similarity	NPC474493
0.7671	Intermediate Similarity	NPC257347
0.7671	Intermediate Similarity	NPC70982
0.7671	Intermediate Similarity	NPC144075
0.7671	Intermediate Similarity	NPC178383
0.7671	Intermediate Similarity	NPC185536
0.7671	Intermediate Similarity	NPC34700
0.7671	Intermediate Similarity	NPC141071
0.7671	Intermediate Similarity	NPC477923
0.7671	Intermediate Similarity	NPC138374
0.7671	Intermediate Similarity	NPC103822
0.7671	Intermediate Similarity	NPC200243
0.7671	Intermediate Similarity	NPC230704
0.7671	Intermediate Similarity	NPC231256
0.7671	Intermediate Similarity	NPC212879
0.7671	Intermediate Similarity	NPC66566
0.7671	Intermediate Similarity	NPC104387
0.7671	Intermediate Similarity	NPC471723
0.7671	Intermediate Similarity	NPC240235
0.7662	Intermediate Similarity	NPC296701
0.7662	Intermediate Similarity	NPC218616
0.7656	Intermediate Similarity	NPC135438
0.7647	Intermediate Similarity	NPC27243
0.7647	Intermediate Similarity	NPC476737
0.7647	Intermediate Similarity	NPC474768
0.7639	Intermediate Similarity	NPC195489
0.7639	Intermediate Similarity	NPC95165
0.7632	Intermediate Similarity	NPC236237
0.7632	Intermediate Similarity	NPC102253
0.7632	Intermediate Similarity	NPC13554
0.7632	Intermediate Similarity	NPC322313
0.7612	Intermediate Similarity	NPC174956
0.7612	Intermediate Similarity	NPC81615
0.7606	Intermediate Similarity	NPC283316
0.7606	Intermediate Similarity	NPC92801
0.7606	Intermediate Similarity	NPC163020
0.76	Intermediate Similarity	NPC6978
0.76	Intermediate Similarity	NPC318136
0.76	Intermediate Similarity	NPC99168
0.76	Intermediate Similarity	NPC230295
0.76	Intermediate Similarity	NPC472342
0.76	Intermediate Similarity	NPC196753
0.76	Intermediate Similarity	NPC76931
0.76	Intermediate Similarity	NPC72507
0.76	Intermediate Similarity	NPC474989
0.76	Intermediate Similarity	NPC11908
0.76	Intermediate Similarity	NPC470396
0.76	Intermediate Similarity	NPC65897
0.76	Intermediate Similarity	NPC205455
0.76	Intermediate Similarity	NPC18603
0.76	Intermediate Similarity	NPC31828
0.76	Intermediate Similarity	NPC312328
0.76	Intermediate Similarity	NPC138621
0.76	Intermediate Similarity	NPC300499
0.76	Intermediate Similarity	NPC302041
0.76	Intermediate Similarity	NPC472501
0.76	Intermediate Similarity	NPC42853
0.76	Intermediate Similarity	NPC186191
0.76	Intermediate Similarity	NPC158662
0.76	Intermediate Similarity	NPC301707
0.76	Intermediate Similarity	NPC253807
0.76	Intermediate Similarity	NPC98386
0.76	Intermediate Similarity	NPC167037
0.76	Intermediate Similarity	NPC137587
0.76	Intermediate Similarity	NPC307965
0.76	Intermediate Similarity	NPC22955
0.76	Intermediate Similarity	NPC244385
0.76	Intermediate Similarity	NPC85346
0.7571	Intermediate Similarity	NPC160209
0.7571	Intermediate Similarity	NPC216460
0.7568	Intermediate Similarity	NPC278091
0.7568	Intermediate Similarity	NPC46160
0.7568	Intermediate Similarity	NPC106364
0.7568	Intermediate Similarity	NPC470362
0.7568	Intermediate Similarity	NPC86305
0.7568	Intermediate Similarity	NPC93662
0.7568	Intermediate Similarity	NPC14112
0.7568	Intermediate Similarity	NPC78067
0.7568	Intermediate Similarity	NPC240604
0.7568	Intermediate Similarity	NPC113733
0.7568	Intermediate Similarity	NPC202642

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC64123 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	2392
0.2-0.3	4151
0.3-0.4	1748
0.4-0.5	381
0.5-0.6	201
0.6-0.7	79
0.7-0.8	17
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7778	Intermediate Similarity	NPD4785	Approved
0.7778	Intermediate Similarity	NPD4784	Approved
0.7746	Intermediate Similarity	NPD4243	Approved
0.7632	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD7645	Phase 2
0.7432	Intermediate Similarity	NPD6942	Approved
0.7432	Intermediate Similarity	NPD7339	Approved
0.7297	Intermediate Similarity	NPD6926	Approved
0.7297	Intermediate Similarity	NPD6924	Approved
0.726	Intermediate Similarity	NPD7150	Approved
0.726	Intermediate Similarity	NPD7151	Approved
0.726	Intermediate Similarity	NPD7152	Approved
0.72	Intermediate Similarity	NPD5275	Approved
0.72	Intermediate Similarity	NPD4190	Phase 3
0.7123	Intermediate Similarity	NPD7144	Approved
0.7123	Intermediate Similarity	NPD7143	Approved
0.7105	Intermediate Similarity	NPD6933	Approved
0.7105	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4195	Approved
0.6986	Remote Similarity	NPD6922	Approved
0.6986	Remote Similarity	NPD6923	Approved
0.6974	Remote Similarity	NPD8264	Approved
0.6962	Remote Similarity	NPD7509	Discontinued
0.6795	Remote Similarity	NPD6932	Approved
0.675	Remote Similarity	NPD6931	Approved
0.675	Remote Similarity	NPD6930	Phase 2
0.6747	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6079	Approved
0.6628	Remote Similarity	NPD5328	Approved
0.6627	Remote Similarity	NPD4786	Approved
0.6625	Remote Similarity	NPD6929	Approved
0.6585	Remote Similarity	NPD4221	Approved
0.6585	Remote Similarity	NPD3667	Approved
0.6585	Remote Similarity	NPD4223	Phase 3
0.6548	Remote Similarity	NPD5329	Approved
0.6543	Remote Similarity	NPD7332	Phase 2
0.6543	Remote Similarity	NPD7514	Phase 3
0.6533	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4788	Approved
0.6506	Remote Similarity	NPD6695	Phase 3
0.65	Remote Similarity	NPD7145	Approved
0.65	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7515	Phase 2
0.6471	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD4519	Discontinued
0.6429	Remote Similarity	NPD4197	Approved
0.6429	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6683	Phase 2
0.6404	Remote Similarity	NPD4202	Approved
0.64	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5360	Phase 3
0.6395	Remote Similarity	NPD3573	Approved
0.6395	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5776	Phase 2
0.6375	Remote Similarity	NPD6925	Approved
0.6353	Remote Similarity	NPD6893	Approved
0.6341	Remote Similarity	NPD4748	Discontinued
0.6341	Remote Similarity	NPD4695	Discontinued
0.6333	Remote Similarity	NPD7748	Approved
0.6292	Remote Similarity	NPD8035	Phase 2
0.6292	Remote Similarity	NPD8034	Phase 2
0.6279	Remote Similarity	NPD4688	Approved
0.6279	Remote Similarity	NPD4690	Approved
0.6279	Remote Similarity	NPD5280	Approved
0.6279	Remote Similarity	NPD4138	Approved
0.6279	Remote Similarity	NPD4693	Phase 3
0.6279	Remote Similarity	NPD5205	Approved
0.6279	Remote Similarity	NPD4694	Approved
0.6279	Remote Similarity	NPD5690	Phase 2
0.6279	Remote Similarity	NPD4689	Approved
0.6265	Remote Similarity	NPD6902	Approved
0.6265	Remote Similarity	NPD6898	Phase 1
0.6235	Remote Similarity	NPD3665	Phase 1
0.6235	Remote Similarity	NPD3666	Approved
0.6235	Remote Similarity	NPD3133	Approved
0.6234	Remote Similarity	NPD4787	Phase 1
0.6207	Remote Similarity	NPD7750	Discontinued
0.6207	Remote Similarity	NPD7524	Approved
0.6196	Remote Similarity	NPD5221	Approved
0.6196	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5222	Approved
0.619	Remote Similarity	NPD388	Approved
0.619	Remote Similarity	NPD386	Approved
0.617	Remote Similarity	NPD5286	Approved
0.617	Remote Similarity	NPD5285	Approved
0.617	Remote Similarity	NPD4696	Approved
0.6136	Remote Similarity	NPD4723	Approved
0.6136	Remote Similarity	NPD4722	Approved
0.6129	Remote Similarity	NPD5173	Approved
0.6129	Remote Similarity	NPD7902	Approved
0.6129	Remote Similarity	NPD4755	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6105	Remote Similarity	NPD5223	Approved
0.6098	Remote Similarity	NPD3617	Approved
0.6094	Remote Similarity	NPD384	Approved
0.6094	Remote Similarity	NPD385	Approved
0.6067	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4753	Phase 2
0.6064	Remote Similarity	NPD7638	Approved
0.6064	Remote Similarity	NPD5290	Discontinued
0.6047	Remote Similarity	NPD3668	Phase 3
0.6044	Remote Similarity	NPD6399	Phase 3
0.6042	Remote Similarity	NPD5211	Phase 2
0.6042	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD5225	Approved
0.6042	Remote Similarity	NPD5224	Approved
0.6042	Remote Similarity	NPD4633	Approved
0.6027	Remote Similarity	NPD368	Approved
0.6022	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD7639	Approved
0.6	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD4700	Approved
0.5979	Remote Similarity	NPD5175	Approved
0.5979	Remote Similarity	NPD5174	Approved
0.5949	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD4758	Discontinued
0.5949	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7087	Discontinued
0.5918	Remote Similarity	NPD5141	Approved
0.5914	Remote Similarity	NPD4629	Approved
0.5914	Remote Similarity	NPD5210	Approved
0.5909	Remote Similarity	NPD5279	Phase 3
0.5909	Remote Similarity	NPD6098	Approved
0.59	Remote Similarity	NPD6899	Approved
0.59	Remote Similarity	NPD6881	Approved
0.5897	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.589	Remote Similarity	NPD1145	Discontinued
0.5882	Remote Similarity	NPD4692	Approved
0.5882	Remote Similarity	NPD4139	Approved
0.5859	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD6402	Approved
0.5859	Remote Similarity	NPD7128	Approved
0.5859	Remote Similarity	NPD6675	Approved
0.5857	Remote Similarity	NPD342	Phase 1
0.5854	Remote Similarity	NPD6117	Approved
0.5824	Remote Similarity	NPD4096	Approved
0.5816	Remote Similarity	NPD4754	Approved
0.5806	Remote Similarity	NPD7900	Approved
0.5806	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4058	Approved
0.5802	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5789	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6883	Approved
0.5784	Remote Similarity	NPD7290	Approved
0.5784	Remote Similarity	NPD7102	Approved
0.5783	Remote Similarity	NPD6116	Phase 1
0.5778	Remote Similarity	NPD4518	Approved
0.5775	Remote Similarity	NPD4219	Approved
0.5769	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6411	Approved
0.5745	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6011	Approved
0.5743	Remote Similarity	NPD4729	Approved
0.5743	Remote Similarity	NPD4730	Approved
0.5743	Remote Similarity	NPD7320	Approved
0.5732	Remote Similarity	NPD3703	Phase 2
0.573	Remote Similarity	NPD7521	Approved
0.573	Remote Similarity	NPD7146	Approved
0.573	Remote Similarity	NPD7334	Approved
0.573	Remote Similarity	NPD6684	Approved
0.573	Remote Similarity	NPD6409	Approved
0.573	Remote Similarity	NPD5330	Approved
0.5729	Remote Similarity	NPD4225	Approved
0.5728	Remote Similarity	NPD6649	Approved
0.5728	Remote Similarity	NPD6617	Approved
0.5728	Remote Similarity	NPD8130	Phase 1
0.5728	Remote Similarity	NPD6869	Approved
0.5728	Remote Similarity	NPD6847	Approved
0.5728	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD4224	Phase 2
0.5714	Remote Similarity	NPD6080	Approved
0.5714	Remote Similarity	NPD5364	Discontinued
0.5714	Remote Similarity	NPD6697	Approved
0.5714	Remote Similarity	NPD6114	Approved
0.5714	Remote Similarity	NPD7331	Phase 2
0.5714	Remote Similarity	NPD6115	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD6118	Approved
0.57	Remote Similarity	NPD4768	Approved
0.57	Remote Similarity	NPD4767	Approved
0.5699	Remote Similarity	NPD5133	Approved
0.5696	Remote Similarity	NPD4137	Phase 3
0.5686	Remote Similarity	NPD6014	Approved
0.5686	Remote Similarity	NPD6373	Approved
0.5686	Remote Similarity	NPD6013	Approved
0.5686	Remote Similarity	NPD6012	Approved
0.5686	Remote Similarity	NPD6372	Approved
0.5673	Remote Similarity	NPD8297	Approved
0.5673	Remote Similarity	NPD6882	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data